Concept explainers
Interpretation:
The reason for the fact that
Concept introduction:
By convention, the terms dextrorotation and levorotation (or laevorotation) represent the movement of plane polarized light clockwise or anticlockwise, respectively, for a compound as seen by the observer whom the light is approaching. The compound exhibiting dextrorotation is said to be dextrorotatory and that exhibiting levorotation is said to be levorotatory.
The dextrorotation and levorotation can be quantized by measuring the degree of specific rotation of the compound,
The value of dextrorotation is positive (+) and that of levorotation is negative (-).
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Organic Chemistry
- (d) Draw the structure of the expected product when monosaccharide B undergo mutarotation upon dissolving in water in the presence of Tollens reagent (AGNO3, NHẠOH). он OH O. OH OH OH monosaccharide Barrow_forwardThe following observations are obtained after a D-hexose was made to react with several reagents: (1) The reactions of a D-hexose with (a) to (d) below yields an aldaric acid (a) NH₂OH, (b) (CH3CO)₂O, NaOCOCH 3, and, (c) NaOCH3, and then, (d) HNO3, H₂O (2) HNO3 oxidation of the same D-hexose gives an aldaric acid. Predict the structures of the three (3) possible hexoses that can undergo the above reactions?arrow_forward1. Draw Haworth projections of B-D-arabinofuranose and a-L-mannopyranose. 2. Consider the structure of the disaccharide drawn at right: НО `CH2 В ОН (a) Give the names and D/L designation for the two monosaccharides linked together. H,C-O OHO „OH OH А: НО НО A В: ОН (b) In the structure, circle the anomeric carbon of each saccharide. (c) Is each saccharide present in its a or ß anomer? Specify both A and B (d) Would this disaccharide undergo mutarotation? Why or why not? (e) Would this disaccharide react with Tollens and/or Benedicts reagent? Why or why not? (f) There are two reasons this is very unlikely to be a naturally occurring disaccharide. What about its structure suggests this is true? Give both reasons.arrow_forward
- Consider the structure of raffinose, a trisaccharide found in sugar beets and a number of higher plants. HO CH,OH Но- OH OCH, Но Но OH НОСН Но CH,OH ÓH raffinose (a) Classify raffinose as a reducing or nonreducing sugar, and tell how you know. (b) Identify the glycoside linkages in raffinose, and clas- sify each as either a or B. (c) Name the monosaccharides formed when raffinose is hydrolyzed in aqueous acid. (d) What products are formed when raffinose is treated with dimethyl sulfate in NaOH, and then with aqueous acid and heat?arrow_forward2. Draw structures for furanose and pyranose forms of D- lyxose. Draw the scheme of a tautomeric equilibrium for D-lyxose (a and b-anomers).arrow_forwardAnswer the following questions. (I narrowed it down to only three subparts)arrow_forward
- 5. Provide suitable responses for questions (a) – (). 6 CH2OH 4 OH OH 3 OH (a) What is the relative configuration of the above monosaccharide? (b) Which labeled carbon is the anomeric carbon? (c) Trace and identify the acetal in the above monosaccharide. (d) Draw the hemiacetal that results from above acetal. (e) Draw the open chain equivalent of the sugar in part (d). (f) Classify the monosaccharide below as a D-sugar or an L-sugar. H. OH O. OH CH,OH OH OHarrow_forwardSeveral compounds have been found to inhibit -lactamase, and drugs based on these compounds can be taken in combination with penicillins and cephalosporins to restore their effectiveness when resistance is known to be a problem. The commonly prescribed formulation called Augmentin is a combination of the -lactamase inhibitor shown below with amoxicillin (shown above). It is used to treat childhood ear infections when resistance is suspected, and many kids know it as the white liquid that tastes like bananas. Which of the statements below are true statements? 1. The stereochemistry of the fusion between the four-and five-membered rings in the inhibitor and amoxicillin are different. 2. The inhibitor possesses enol ether and allylic alcohol functional groups while the antibiotic possesses a phenol and a secondary amide functional group. 3. Neither the inhibitor nor the antibiotic contains strained rings. 4. Both 1 and 2 are true.arrow_forwardRegarding 4-O- (α-D-psychofuranosyl) -β-D-allopyranose. Please indicate the RIGHT alternative: (a) The disaccharide reacts with CH3OH in an acid medium to form a glycoside that cannot be oxidized with HNO3. (b) It is a reducing disaccharide only in basic medium. (c) In the structure there is only one glycosidic bond that is of the type β 1-O-4 ' (d) The hydrolysis products of this disaccharide do not show mutarrotation. (e) The disaccharide structure contains two six-membered rings.arrow_forward
- The anticoagulant heparin is a polysaccharide that contains alternating residues of -D- glucuronic acid-6- sulfate and N-sulfo-D-glucosamine-6sulfate connected by (1 B 4)- glycosidic linkages. Draw a part of heparin that shows one each of the two residues.arrow_forward4. Identify the component monosaccharides of each of the following compounds and describe the type of glycosidic linkage in each. Но он Но OH HO он Но- Но- (a) OH (c) CH,OHO. (b) CH2OHO Lon OH HO H ČHOH H OH ÓH ОНarrow_forward(d) Use the diagram below to complete the cyclic alpha form of structure V (e) Circle the hemiacetal in cyclic alpha form of structure V. (f) Redraw the cyclic alpha form of structure V but replace the OH group on the anomericcarbon with a methoxy group. Is this modified monosaccharide a reducing sugar or anonreducing sugar?arrow_forward
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